Hunsdiecker Reaction is an Organic Reaction Named after a German Chemist Heinz Hunsdiecker. Learn about Hunsdiecker Reaction Mechanism with the Help . The Hunsdiecker Reaction is the reaction of a silver carboxylate with a halogen to form an The reaction involves a radical chain mechanism. Analogous to the Kolbe electrolysis reaction, the Hunsdiecker reaction (after Heinz Hunsdiecker, born in ) is a decarboxylation with a radical intermediate.

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The reaction was first demonstrated by Alexander Borodin in his reports of the preparation of methyl bromide from silver acetate.

Hunsdiecker reaction

Why are alkenes and alkynes more reactive? Email Required, but never shown. Silver carboxylates, required as starting products for the Hunsdiecker reaction, may be obtained through conversion of the corresponding carboxylic acid with silver oxide.

Common knowledge holds that primary radicals form less readily than higher ones to the point where it does not happen at all. Sign up using Facebook.

The main driving force of this reaction step is the precipitation of the extremely poorly soluble and stable silver bromide. The weak “O-Br” bond undergoes homolytic cleavage to form an acyl radical 3.

Hunsdiecker Reaction

I’m attaching the reaction mechanism for reference. The chain initiation is the homolytic cleavage of the relatively weak oxygen-bromine bond. About the Learning Unit Authors Dr. Why are alkenes and alkynes called unsaturated compounds? From Wikipedia, the free encyclopedia.


Substitution reactions Free radical reactions Halogenation reactions Name reactions. The bromine reacts with the silver carboxylate 1 to give an unstable acyl hypobromite 2.

CS1 German-language sources de. Impact of this question views around the world. The resulting alkyl radical, or hydrocarbon radical, abstracts a bromine atom from a further acyl hypobromite molecule.

The reaction mechanism of the Hunsdiecker reaction is believed to involve organic radical intermediates. Home Questions Tags Users Unanswered. Raoul Kessels 3, 2 Hunsdieckker is now well established that mercuric oxide can also be used to effect this transformation. Hunsdiecker reaction follows free radical mechanism but it is given that hunsdieker of reaction with different alkyl groups R attached to silver salts of carboxylic acid follows the order as follows.

Could you elaborate why such radicals form here?

The silver salt of the carboxylic acid 1 will quickly react with bromine to form acyl hypohalite intermediate 2. The Hunsdiecker Reaction is the reaction of a silver carboxylate with a halogen to form an alkyl halide. Ritwik Das 5 There are several variations of the Hunsdiecker reaction that are known, in which silver I carboxylate is, for instance, exchanged for thallium I carboxylate, or in which the carboxylic acid is directly treated with a combination of lead tetraacetate and halide ions chloride, bromide, or iodide.

Hunsdiecker Reaction

Chemische Berichte in German. Mithoron 3, 8 28 reactiln So once the system is started, the propagation step 4 will proceed faster for primary radicals. Alexander Borodin first observed the reaction in when he prepared methyl bromide from silver acetate. The Hunsdiecker hunsdieckker also called the Borodin reaction or the Hunsdiecker—Borodin reaction is a name reaction in organic chemistry whereby silver salts of carboxylic acids react with a halogen to produce an organic halide.


Initiation The bromine reacts with the silver carboxylate 1 to give an unstable acyl hypobromite 2. Formation of the diradical pair 3 allows for radical decarboxylation to form the diradical pair 4which will quickly recombine to form the desired organic halide 5.

Through the application of hunsfiecker reagents carboxylic acids are converted into alkyl chlorides and alkyl iodides, as well.

Reactions of Carboxylic Acids – Chemgapedia

Chemistry Stack Exchange works best with JavaScript enabled. Views Read Edit View history. The Hunsdiecker reaction takes place when a silver carboxylate is heated in C Cl 4 in the presence of bromine. Post Your Answer Discard By clicking “Post Your Answer”, you acknowledge that you have read our updated terms of serviceprivacy policy and cookie policyand that your continued use of the website is subject to these policies.